Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.
The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditi...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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2011
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| _version_ | 1826295002056097792 |
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| author | Fletcher, S Solà, J Holt, D Brown, R Clayden, J |
| author_facet | Fletcher, S Solà, J Holt, D Brown, R Clayden, J |
| author_sort | Fletcher, S |
| collection | OXFORD |
| description | The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established. |
| first_indexed | 2024-03-07T03:54:24Z |
| format | Journal article |
| id | oxford-uuid:c25ceb9b-9fc4-472d-818c-1774ed1bc6ad |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:54:24Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:c25ceb9b-9fc4-472d-818c-1774ed1bc6ad2022-03-27T06:08:27ZSynthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c25ceb9b-9fc4-472d-818c-1774ed1bc6adEnglishSymplectic Elements at Oxford2011Fletcher, SSolà, JHolt, DBrown, RClayden, JThe method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established. |
| spellingShingle | Fletcher, S Solà, J Holt, D Brown, R Clayden, J Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title | Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title_full | Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title_fullStr | Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title_full_unstemmed | Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title_short | Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. |
| title_sort | synthesis of enantiomerically enriched r c labelled 2 aminoisobutyric acid aib by conformational memory in the alkylation of a derivative of l alanine |
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